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1. Scott Kraft had his own theory about why Sophia kept herself so busy. What do you think the reason was and how does that tie in, if at all, to Sophia’s overall development as a character?

2. How would Jack Wynn from World Partners have treated Sophia differently if she had been a man? 

3. In your opinion, did Sophia’s sister Audrey choose the “right” life approach and/or path in life?

4. Which character is more aspirational: Sophia or Audrey?

5. How do you think Sophia managed to navigate the predominantly male work environments she encountered while still holding true to her gut and personality?

6. Consider some of the sticky situations Sophia had to navigate in her personal and professional lives. What is your assessment of how she handled some of them and why do you think she responded the way she did?

7. Throughout the novel, Sophia clearly struggles with balancing her career and personal life. What would you have done if you’d been in her shoes?

8. How do you respond to the question: “Is it possible for a woman to fulfill a traditional role while still being as successful as Sophia was?”

9. How would you respond if your manager / boss gave you the choice that Rajesh gave Sophia: take another airplane or get fired?

10. How did you feel about Sophia at the beginning of the book? Did your feelings about her change by the end of the book; if so, why?

11. Who was your favorite character in the novel and why?

12. What part of the novel caught you most by surprise?

13. Who was the best role model for Sophia?

14. How did you feel about Peter and Daniel? Did you sympathize with either or both?

15. Who was the greater visionary: Scott Kraft or Andre Stark?

16. Summarize the cultural differences between the workplaces of Ion and Treehouse. Which company would you have preferred to work at?

17. In Chapter 5, Sophia is delighted that for once in her life, she's not the cute one, the sick one, or the Chinese one. She's Grant Vickers "super paralegal."  In what way do you find yourself being defined, and how do you feel about it? 

18. How do you think about the role Sophia's parents (especially her mom) played in her approach to business and her career? To what degree did they help? And did they hurt in any way?

19. Andre and Scott are both strong and difficult men who made history.  In your mind - based on the book and what you know of each of them - how are they similar? how are they different?

20. While Andre and Scott are both difficult, demanding leaders, Sophia has a uniquely different experience with Scott vs. Andre.  What is true about each of the men that created Sophia's experience? And what is true about Sophia, and when she encountered each of one of them in her career, that might've influenced her experience?

21. Jonathan buys Sophia a gift that read "Fortune Favors the Bold" - a phrase which describes many of the characters in this book. Talk about the role of "boldness" in the success of the characters in this book.